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Synthesis and odour evaluation of stereoisomers of octahydrobenzopyran derivatives

✍ Scribed by Pablo J. Linares-Palomino; Sofía Salido; Joaquín Altarejos; Manuel Nogueras; Adolfo Sánchez

Publisher
John Wiley and Sons
Year
2006
Tongue
English
Weight
306 KB
Volume
21
Category
Article
ISSN
0882-5734

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✦ Synopsis

The synthesis and isolation of the four racemic 2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydro-2H-1benzopyran stereoisomers from β β β β β -ionone and α α α α α -ionone is reported. It was based on the cyclization of dihydro-β β β β β -ionone and dihydro-α α α α α -ionone with chlorosulfonic acid at low temperature to yield stereospecifically the trans-fused and cis-fused hexahydrobenzopyran derivatives, respectively. The direct cyclization of dihydro-β β β β β -ionol and dihydro-α α α α α -ionol under iden- tical conditions was also explored. In addition to the complete spectroscopic characterization of every isolated isomer, a description of their olfactory properties is displayed.

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